Chloride → 1-(2,3-Dihydro-5-benzofuranyl)ethanone

HRID 1038519Notes

Reaction equation

HRID 1038519 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1.[C:10](Cl)(=[O:12])[CH3:11].[Cl-].Cl>ClCCl>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10](=[O:12])[CH3:11])=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 312ChlorideHCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 10329Dihydrobenzofuran

Product 1

HCID 1452201-(2,3-Dihydro-5-benzofuranyl)ethanoneYield 99.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

2,3-Dihydrobenzofuran (10 g, 83.2 mmol) was dissolved in dichloromethane (400 mL), added sequentially with acetyl chloride (11.8 mL, 167 mmol) and alminium chloride (33.3 g, 250 mmol) at −10° C., and the mixture was stirred at −10° C. for 0.5 hours. The reaction solution was added 5% aqueous solution of hydrochloric acid, extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. 1-(2,3-Dihydrobenzofuran-5-yl)ethanone (13.4 g (yield 99%)) was obtained as a colorless oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-338de7a146ab4243b23cf0cb65e4630f
Source dataset
uspto-grants-2013_10
Patent number
US08551985B2

Reaction notes

Loading…